Synthesis of oligosaccharins: a chemical synthesis of propyl O-beta-D-galactopyranosyl-(1----2)-O-alpha-D-xylopyranosyl-(1----6)- O-beta-D-glucopyranosyl-(1----4)-beta-D-glucopyranoside.
Condensation of allyl 3,4-di-O-benzyl-beta-D-xylopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of silver triflate gave allyl 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-galactopyranosyl)-3,4-di-O benzyl-beta-D-xylopyranoside (7, 83%). Compound 7 was converted in five steps into 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-xylopyranosyl bromide (13), which was condensed immediately with allyl 2,3,6-tri-O-acetyl-4-O-(2,3,di-O-acetyl-beta-D-glucopyranosyl)-beta-D- glucopyranoside to give crystalline allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranosyl)- (1----2)-O-(3,4,-di-O-benzyl-alpha-D-xylopyranosyl)-(1----6)-O-(2,3,-di- O-acetyl-beta-D-glucopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-beta-D-gluco pyranoside (23, 50%). O-Deacylation of 23 followed by catalytic hydrogenolysis gave the title glycoside.
Wotovic
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Laboratoire de Biochimie Structurale, U.R.A. 499, U.F.R.-Faculté des Sciences, Université d'Orléans, France.
Jacquinet
J C
JC
Sinaÿ
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D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010944:Plants / Q000032:analysis / Q000187:drug effects
D006027:Glycosides; D009844:Oligosaccharides; C067063:propyl O-galactopyranoysl-(1-2)-O-xylopyranosyl-(1-6)-O-glucopyransoyl-(1-4)-glucopyranoside